


Through All These Years

by Why_do_you_want_to_know



Category: Supernatural
Genre: Adopted Children, Alternate Universe - Human, Alternate Universe- No Supernatural, Asexual Castiel (Supernatural), Asexual Character, Bisexual Dean Winchester, Boys Kissing, Castiel/Dean Winchester First Kiss, Cute Kids, Dean Loves Halloween, Dean Winchester Uses Actual Words, Dean doesn't care, Dean is a Good Friend, Dean is a cute child, Dean is good at baking, Getting Together, Good Older Sibling Gabriel (Supernatural), Good Older Sibling Lucifer (Supernatural), Good Older Sibling Michael (Supernatural), Good Parent Mary Winchester, Growing Up Together, Halloween, Halloween Costumes, Halloween parties, He's cool, Kissing, M/M, Making Friends, Never Have I Ever, Pumpkin carving, Sam Winchester Has Puppy Dog Eyes, Sam is cute, Then Grow Up, Trick or Treating, Underage Drinking, actual communication, matching costumes, so is Cas - Freeform, they start as children, zombie pirates
Language: English
Status: Completed
Published: 2020-10-31
Updated: 2020-10-31
Packaged: 2021-03-09 00:00:39
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 7
Words: 8,381
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27315181
Author URL: https://archiveofourown.org/users/Why_do_you_want_to_know/pseuds/Why_do_you_want_to_know
Summary: They meet Halloween of 1985.They wear matching outfits Halloween of 1988.They do pumpkin carving Halloween of 1991.They come out to each other Halloween of 1994.They go to a party Halloween of 1997.They get together Halloween of 1998.They have a happy Halloween of 2020.Follow Castiel Novak and Dean Winchester as they spend Halloween together. From meeting to domestic bliss.
Relationships: Castiel/Dean Winchester
Comments: 8
Kudos: 41





	1. 1985

**Author's Note:**

> I am so bad at summaries, but you get the idea...  
> I had this idea last night after realising I had nothing to post for Halloween or for Ace week, did my best to write it today, and clearly it went well seeing as I have 7,000 words written and only one chapter left.  
> And yes. I do want to die after writing that much in one day. But it's okay, it's Halloween in 2020, what else would I be doing?  
> I actually loved writing this, and I hope you enjoy reading!!  
> I will do my best to get this all up before I go to sleep!! So before Halloween is over.

**31st October, 1985**

Dean pulled on his mother's hand, all but dragging her down the street and towards the next house which was covered in Halloween decorations. He absolutely adored trick or treating, and actually the entire day. Halloween was probably his favourite holiday, and every single person they passed could see it just from the excitement in his face and the way he was walking as quickly as his little legs would take him.

"Come on Mom," he giggled, jumping up and down and making the metal pieces on his cowboy costume rattle, "I want to get all the candy possible!"

Mary laughed, having to quick walk to keep up with her eldest son, while holding little Sammy who was dressed up as a pumpkin, but had gotten tired of walking about fifteen minutes before. She was surprised he'd lasted so long, he was only small, and Dean was definitely not being considerate for anyone who wasn't as excited as he was.

"We're going to have to head soon, Dean," she warned, readjusting Sam in her arms, glancing at her watch and seeing how close to Dean's bedtime it was getting.

"I know, but can we go to just a few more houses! Please." Mary couldn't say no to his puppy eyes, especially not on Halloween.

"Alright then. Just to the end of this row. Then we're going home."

"Thank you, thank you, thank you," he gasped, already rushing down the driveway of the next house.

A sudden gust of wind blew down the street, making all the parents standing around with small children shiver, and knocking Dean's cowboy hat off his head. It flew through the air for a little bit, before dropping it just along from them. Dean threw himself after it, but before he could grab it, someone else did.

"My hat!" he cried out, in that way only little kids can, assuming that this was it, his hat was being stolen and he would never see it again.

"Here you go." A slightly older boy stood in front of Dean, probably only a year older, but it was a bit too dark to see properly, wearing fluffy white angel wings and a shy smile. "I take it this is yours?" He held out the cowboy hat.

"Yes it is!" Dean cheered, his smile only growing when the other boy dropped the hat back onto his head. "I'm Dean, what's your name?"

"I'm Castiel," the other boy replied, looking slightly confused over why Dean was still talking to him.

"Castee- Catst- can I call you Cas?"

"That- that works," Castiel replied, his eyes wide. As though never been given a nice nickname before. "My brothers call me Cassie," he told Dean, "but I think that's mainly because they knew I hate it.

"Cas it is then," Dean decided, smiling happily at his new friend. "Do you live around here Cas?"

"Yes actually, just a few minutes that way," he pointed along the street, in the general direction of Dean's house.

"Me too!" Dean gasped like it was the most exciting thing that had happened all week, "Maybe we live near each other!"

"Maybe," Cas agreed, shuffling his feet awkwardly and reaching back to fiddle with his costume wings.

"Come on Dean," Mary called kindly, a half asleep Sam still cradled in her arms, "time to carry on. Is your new friend coming with us?"

"Can you? Can you? Can you?" Dean asked, back to bouncing in place fast enough that his hat kept on bouncing on his head and nearly falling off.

"I'll have to ask my brothers," Cas said slowly, looking behind him at a small group of other boys, who Dean would guess were between ten and sixteen.

"I hope they let you," Dean said, sounding as hopeful as he felt. He didn't know Cas well, but he could tell that he was nice, and he definitely wanted to get to know him more. He talked weirdly, but there was something endearing about him, and Dean's six year old brain instantly latched on and called him friend.

"I hope so too," Cas replied, his blue eyes wide and full of truth. He walked away then, going to talk to his brothers. Dean saw him point over at him, and at him Mom, and then they were all coming over, the older two going to talk to Mary, while the younger one - he was still older than Dean mind - came to talk to him.

"Heya there Dean-o," he grinned, apparently even more forward than Dean himself was. "I'm Gabriel, I take it you've decided to adopt my baby bro."

"You're three years older than me Gabe," Cas muttered under his breath, but Dean could hear the fondness in his tone, and he instantly knew he had to be polite to this guy if he wanted Cas to be his friend.

And he really did want Cas to be his friend.

"Yes, I have." Dean said, nodding his head, "Cas is my friend now."

Gabriel turned to Cas, as though he didn't fully believe Dean's story. "It's true," Cas sighed, nearly pulling a feather out of his wings as he rolled his eyes at his brother, "I want to be his friend Gabe, you can stop your overprotective big brother act."

"I just want to keep little Cassie safe and this is the thanks I get!" Gabe replied dramatically, but he did smile at Dean before walking back to stand with his other brothers, so Dean guessed that meant he passed.

"Come on Dean and Castiel," Mary called, "we're going now. We are going to drop Castiel off at home on our way back, okay?"

Dean and Cas shared an excited look, running to catch up with Mary. Although Dean was still excited about the candy, he was almost even more excited about finding out where Cas lived. Dean hoped that Cas would be very close to his house, so they could meet up and play, and be best friends forever.

Castiel was hoping for a similar thing.


	2. 1988

**Notes for the Chapter:**

> I asked my sibling for a super cool Halloween costume idea, all they gave me was 'slug' so here we are. You get Zombie Pirates. And yes, this chapter does say Zombie Pirates way too many times.

**31st October 1988**

"Come on Gabe!" Castiel called for his brother. He'd been standing at the front door for at least the last five minutes, waiting for his older brother. He was going trick or treating with Dean's family this year, but apparently he wasn't allowed to walk to Dean's house alone in the dark, so he was having to wait for Gabe to come and walk with him.

Sometimes he hated how overprotective his family was.

"For the last time I'm coming!" Gabe yelled back, finally emerging from his room in a full vampire costume. Castiel was still in his normal clothes, he was getting changed at Dean's - they were going to wear matching outfits - but apparently Gabe had decided wearing normal clothes outside on Halloween was an unfathomable.

"You say that as though I haven't been waiting for the last ten minutes."

"Yeah yeah," Gabe waved his words away, as though it was no big deal, "come on then, we can do now."

"Finally." Castiel threw the door open, walking as quickly as he could down the street and towards Dean's house, smiling at the small groups of trick or treaters who were already out, most of whom were small children with their parents due to the early hour.

"Slow down a bit Cassie!" Gabe yelled from behind, not walking anywhere near as quickly as Castiel was. "This isn't a race or anything."

"Don't whine Gabe," Castiel laughed, "I'm walking slowly, clearly you need to go to the gym more." Gabe's annoyed face just made Castiel walk even faster, laughing all the way.

"I hate you!"

"Love you too," Castiel giggled, turning to the left and walking up Dean's driveway. "Are you coming in?"

"Yeah I might as well," Gabe shrugs, "Mary makes the best food, and you can bet in not going to kiss out on her Halloween goodies." Castiel rolled his eyes, again, but secretly he agreed. Mary couldn't cook anything, but she was an amazing baker, and whenever Dean helped her everything became even better.

They walked in together, Gabe instantly following his nose to the kitchen, while Castiel walked upstairs and walked into Dean's room.

"Hey Dean, you ready?"

"Got it all right here," Dean waved his hand at his bed which was covered in what would soon become his Halloween costume, stage make-up and everything.

"Me too," Cas shook the bag he was still holding, his contributions to their costumes rattling away inside.

"Alright," Dean grinned, "let's get this party started!"

Twenty minutes later and they were both ready, matching yet different zombie pirates. Dean had a hook on one hand, and Castiel had a toy slug on his shoulder, because apparently Dean couldn't find any parrots. Their faces were a strange grey green colour, and the clothes they had on were ripped. Castiel knew they looked awesome.

"This was actually a good idea," he grinned into the mirror where they stood side by side, turning around to make sure they had everything right. Castiel had originally thought that maybe doing both zombies and pirates would be a bit too much, but it actually worked really well.

"I told you it would be!" Dean laughed, trying to figure out how to hold a bag for his candy, without giving up his hook hand, and still being able to use a hand.

"Yeah, yeah, you were right," Castiel saw Dean's face bright up and his mouth open and Castiel could just tell what he was about to say. "For once." Castiel continued before Dean could get any words out. "I know what you're about to say, and no. You're not always right. This is the exception, not the rule."

Dean laughed, apparently not caring about basically being insulted by his best friend. "That's why we're friends after all, I need someone to be my logic filter."

"I'm glad to know I have some use," Castiel sighed, folding his normal clothes up and putting them in his bag.

Dean didn't say anything more, just shoulder checked Castiel and headed out his room to go downstairs. Castiel followed, of course he did, and they ended up in the kitchen with Gabe, Mary, and Sam, all of them eating some of the baked treats which were sat on the table.

"There you are boys," Mary smiled, "don't you two look handsome!"

"Mom," Dean groaned, grabbing a pumpkin shaped cookie and flopping into a chair. "We are zombie pirates. Not handsome."

"I don't know why you can't be both."

"I agree with Mary," Cas told his friend, grabbing himself a gingerbread vampire which he could tell had been decorated by Dean. He could just tell these things. "We are very handsome zombie pirates."

"Speak for yourself," Dean muttered under his breath. Castiel wanted to ask him what he meant, but the conversation had already moved on and he would be making too big a deal of it if he asked now.

_ It's nothing  _ he told himself,  _ just a joke, that's just how Dean is. _

"Come on boys, I want pictures," Mary decided, stand up against that wall, let me see your best zombie pirate faces."

"Come on Mom, we're too old for this," Dean sighed, leaning back in his chair and grabbing a new cookie. Castiel wanted to argue that Dean was nine, and definitely not too old for this, but he knew there were better ways to get his friend to change his mind.

"You just know I am a better zombie pirate than you," Castiel taunted, "and you don't want it caught on camera."

It worked like a charm.

"You're not a better zombie pirate than me!" Dean gasped, scandalised, "come on mom, grab your camera. I need proof for the rest of forever that I am the best zombie pirate."

Gabe chuckled from his place at the table, and Mary ginned thankfully, but Castiel wasn't paying attention to them, all of his focus locked on his friend as he tried to twist his face into the scariest face he could imagine.

That day, three years ago exactly, when Castiel first met Dean, continued to be the best day of his life so far. He didn't even want to know how different his lie would be if that gist of wind hadn't sent Dean's hat flying.


	3. 1991

**31st October 1991**

Dean grabbed his coat, slipping out the door before Sam could realise he was going. Sam was desperate for Dean- and maybe Cas too - to go trick or treating with him, like they had the year before. Dean didn't mind going with Sam, and he knew Cas didn't mind either, but they had already planned to go pumpkin carving with Cas' family, and Dean was really looking forward to it.

So now he was sneaking out.

Sue him, Sam's puppy dog eyes were more powerful than Dean okay, so he had to find any way around it that he could. And maybe his way was a little but underhand and sneaky, but so was using puppy dog eyes when someone has already told you that they are sorry, but they can't.

He kept on sneaking until he was down the street from his house, at which point he broke into a run, racing to Cas' house, excitement singing in his veins.

"You ready?" Cas asked with a laugh, throwing the door open before Dean could even start reaching for it. Clearly his friend was just as, if not more, excited as Dean was about this.

"Of course," Dean replied, clapping his gloved hands together and gesturing to his scarf. "I have everything I need. Are you and your family ready?"

"Almost," Cas pulled the door open further, stepping back so that Dean could step in, "Michael is driving us, we just have to wait for him to grab his shoes." Dean nodded, leaning against the nearest wall and smiling at his friend.

"What are you going to carve onto yours?" he asked, knowing that his friend would have been planning it for the last week at the very least, and probably had a couple of sketches of his plan in his room. Dean was planning to just wing it, but Cas was way too responsable, and way too arty, to just do that.

"I'm stuck between a witch, and a dragon," Cas replied, staring at the wall next to Dean's head, a distance in his eyes that Dean could tell was him imagining each design on a pumpkin.

"I can see your problem," Dean whistles, "a witch is more Halloweenie, but a dragon is so cool."

"Exactly!"

"Could you flip a coin?"

"Maybe," Castiel dropped his head back against the wall, "but I want to do both!"

"Could you do-" Dean thought carefully. This meant a lot to Cas, no matter how small a thing it was, and Dean wanted his friend to be happy. "Could you do one on each side?"

"Would that work?" There was excitement in Castiel's eyes now. He was clearly hoping Dean's idea would work, and Dean hoped it would too.

"I don't see why not. People do those good cop, bad cop, things all the time. This wouldn't be that different."

"It wouldn't be the same," Cas mused, "but that doesn't mean it wouldn't work."

"What are you two talking about?" Gabe asked, jumping down the stairs, followed by both Michael and Luke.

"Pumpkin designs."

"Of course you are," Gabe looked thoughtful for a moment, turning to talk to Luke. "Do you think they'll kick us out if I carve a dick?"

"Maybe," Luke looked thoughtful, "you could try?"

"Please don't." Michael sounded as tired as he looked, probably only a couple of seconds away from hitting his head off the wall. He'd been looking after his brothers most of his life, their parents were busy and so as the eldest, Michael took responsibility whenever it was needed. He'd been doing it a long time, but Luke and Gabe still managed to catch him on the wrong foot and freeze in shock more often than he would want people to think. Dean understood how he felt, he'd kept an eye on Sam for years, yet he still found himself shocked when Sam did something particularly random.

"We'll see," Gabriel said after a long moment, skipping out the door and leaving everyone else staring at the still open door.

"He's not really going to do it, is he?" Dean asked, even though everything he knew about Gabriel told him that yes, if Gabe wanted to, he would.

"I don't know," Castiel sighed, turning to walk out the door to join Gabe in the car. "We will all just have to hope not."

The drive was fairly quiet, but there was enough low level conversation to stop it from being awkward. Cas and Dean spent most of it whispering between themselves about nothing at all, just random things that came to their minds, catching up from the last week, ranting about TV shows. The kind of easy conversation which only best friends could manage.

"Come on you assholes," Michael sighed, parking the car but not climbing out straight away. "Please don't get us thrown out." Dean saw him make eye contact with Gabe in the rear-view mirror, and could easily tell that his warning hadn't been directed to either Cas nor Dean. And even Luke was hopefully old enough not to sneak in with something stuoid mid carving.

It really was never a dull moment with Cas' family.

"Alright, let's get this over with," Luke sighed, though if the speed he walked towards the building hosting the carving event - they had special tools and apparently from Cas, you hadn't truly carved a pumpkin unless you've done it at one of these places at least once - was anything to go by, he was pretty excited to get to carve his pumpkin.

"How many people are going to be here at the same time as us?" Dean whispered as they walked across the parking lot. He wasn't shy, not at all, but he was wondering how busy the small building would be.

"Not very many," Cas shrugged, apparently unbothered, "it's only a small event, and all the people with little kids will have gone earlier in the day. We sometimes end up in here on our own on the quieter years."

Dean nodded, his shoulders relaxing. He already felt like he had to act differently around Cas when there were too many people around, he couldn't explain it, but it was how he felt, so the fact it was almost definitely going to be quiet was a relief of sorts.

They walked inside, breathing a sigh of relief at the warmth, the bright lights making them all squint.

They were given some tools, told to pick a pumpkin, and sent off. Dean spied one other tiny family, but they were clearly just finishing, so Dean wasn't too worried about that, focusing on picking the perfect pumpkin for him to maul.

"Which one should I pick?" Gabriel asked, a smirk on his face as he held up the two most misshapen pumpkins Dean had ever seen. He was absolutely certain that Gabe had purposefully searched for them specially for their ugliness, but that was just Gabe, nothing special.

"The one which looks most like your face." Michael sighed.

"Hmmmm, this one." Gabe picked the more deformed one, winking at Michael on his way past.

One by one they all picked their perfect pumpkin and picked a table to start gutting them on. It wasn't like Dean had never gutted a pumpkin before, he did it nearly every year, but that would never change how disgusting it was. It was so slimy.

And it only got worse when Luke decided to fire seeds - still sticky with pumpkin guts - at everyone. Just subtly enough to not get caught by the owner of the place.

"I hate you." Dean sighed, not even looking away from his scooping.

"I need a new family." Michael decided, grabbing his tool to start carving the face of his pumpkin, and looking like he meant every word.

"What do you think?" Cas asked, twisting his pumpkin so that Dean could see the design he had sketched onto one side.

It was amazing.

Dean couldn't believe his friend had drawn that, even though he knew how good Cas was at drawing. The dragon was up on its hind legs, breathing fire and flapping it's mighty wings. Dean could tell that Cas was going to have to carve it carefully so that he didn't cut any of the wrong bits.

Dean knew Cas would be able to do it.

"It's amazing Cas! I can't wait to see the finished pumpkin!" Dean gushed, "and I'm sure the witch will be just as amazing!"

"Thank you Dean," Cas smiled fondly. "I look forward to seeing what you do as well."

"Mine won't be anywhere near as good," Dean replied quickly, "I was just going to see if I could do some kind of basic face."

"I'm sure it will be amazing whatever you do." Castiel said with a shrug, and Dean couldn't find it within himself to argue. He'd just have to make sure to make Cas proud.


	4. 1994

**Notes for the Chapter:**

> This one chapter is what started the entire fic. This was how my brain told me to incorporate Halloween and Ace week. So here we are.

**31st October 1994**

Castiel was shaking. He shouldn't be this nervous, Dean was his best friend, nothing would change that - Dean had promised - but maybe this would. Dean's promises didn't count for anything when he didn't know the full story, and maybe when he knew it he would rethink it all.

It would hurt, but Cas wouldn't stop him. He just wanted Dean to be happy, and if never talking to Cas again would help with that, then so be it.

He breathed deeply. He could do this. He could-

"Oh hey Cas, Dean's in his room," Sam said with a friendly smile, stepping back to let Castiel into the house. He breathed deeply, trying to calm himself down. He was way too anxious about this if the way Sam opening the door had made him jump was anything to go by. He needed to breath, calm down, and just do this, and if Dean tried to eat rid of him then he would deal with that when it happened.

They had been friends for nine years, nearly a decade.

This wouldn't change anything.

"Thanks Sam," Castiel said with what was supposed to be a smile but felt more like a grimace, "are you going trick or treating today?"

"Yes I am! Are you?"

"I don't think so. Dean was making movie night noises, so we will probably just stay in and eat our own candy. I brought some, and will share it with you if you're still around." 

Sam grinned, "thank you!"

"No problem," Castiel said, turning to walk up the stairs to head to Dean's room, his smile dropping slightly the closer he got to Dean's room. It felt- wrong. To put it simply. Halloween was Dean's favourite holiday, and all of Castiel's memories of their Halloweens together were so happy.

And yet here he was, shaking in nervous fear because he had no idea how Dean was going to react.

Castiel was asexual. Ace. He didn't feel any sexual attraction towards anyone, and didn't think he ever would. He was sixteen, he'd been thinking about this for a long time, and so of course he was going to come out to his best friend first.

But he didn't know how Dean would react.

He didn't know Dean's opinion on the LGBT+ community, or know if he knew what ace was, or think ace existed, or believe they were part of the community or-

He didn't know any of it. And his mind would not stop it with the worst case scenarios. He'd seen enough hate online that he knew a lot of people didn't accept people like him.

And even if Dean did accept him, there was a high likelihood that he would have to give a vocab lesson over what ace even meant before Dean would understand.

"Cas? I heard the door, you out there?"

Castiel was unable to hold back his slight laugh. Trust Dean to break him out of his spiralling with his innocent confusion.

"I recognise that laugh! I know you're out there Cas!" Dean yelled through the door, apparently not bothering to stand up to find Cas, he was that certain in his laugh recognition.

"Just coming!" Cas called back, taking another moment to breathe before pushing Dean's door open, finding the younger boy flipping through some DVD's, lounged out on his bed. "Hello Dean."

"Heya Cas," Dean grinned, looking up for long enough to make eye contact for a long moment before he returned to his previous task. "What's your favourite Halloween movie?"

"Does Nightmare Before Christmas count?" Cas asked hesitantly, stepping into the room and selling himself into Dean's desk chair.

"Barely, that's more a November movie," Dean replied, "which is your actual favourite?"

"I was being serious. That's the only one I can think of," Cas shrugged, already knowing how Dean was going to react.

"What." Dean seemed to freeze in place, his mouth going slack and his eyes going wide as he just stared at Castiel. "You've never seen any Halloween movies?" His voice was little more than a croak, as though Cas had just told him that his world was crashing down around them.

Cas was unable to hold back his laugh. Dean was an absolute dumbass, and he seriously wondered why he was even friends with such a dramatic idiot.

"I don't know why you're so confused. You know my "pop culture knowledge" is "lacking"."

"Air quotes!" Dean pushed out between even more laughter. "You just- used air quotes."

"It's like you've never met me!" Cas sighed, but he was leaning forwards in his seat, just a few scant inches away from Dean.

"You've got a point. I'm starting to think I really don't," Dean collapsed back so he was lying down, staring helplessly at the ceiling. "You've never seen any Halloween movies!"

"Why is this hurting you so much?" Castiel laughed again, "I don't know any of these movies yet, which just means you get the chance to introduce me to them all." Castiel watched as Dean's face lit up. Clearly he agreed with Cas on that one.

"You make a good point," Dean said thoughtfully, slowly sitting up, "let's go. I want to introduce you to as many movies as I can before the end of the night!"

Cas smiled, but the weight in his chest reminded him of what he still had to do. If he didn't do it today he knew he would wuss out, like he had been doing for the past week, and however scared he was, he really did want to tell Dean. He wanted one less place where he had to hide who he was, and he wanted Dean's support behind him when he eventually came out to some other people.

He'd promised he would do it this week. During Ace awareness week. And now it was the last day and he still hadn't done it yet.

"Dean! Wait." Dean froze halfway off the bed, all of his attention instantly glued onto Cas. "I need to tell you something." Cas continued, his eyes dropping to the floor while Dean situated himself back onto the bed.

He was really going to do this.

He breathed carefully, trying to calm his racing heart. It was okay. He could do this.

"I've been trying to tell you all week, but I keep not going through with it because I'm a coward, but I need to tell you."

"Tell me what? Cas, are you okay?" There was panic in Dean's voice. Pure panic.

"I'm fine, it's nothing bad," Cas assured his friend, wanting to reach out and put a hand on his shoulder to calm him down, but also way too scared to touch his friend right now.

"So what is it?"

"I'm-" Castiel breathed carefully. Now or never. He could do this. "I'm asexual."

The room was silent for a minute, Dean just staring at Cas while Cas stared back.

"It means I-"

"I know what it means," Dean cut Cas off, what sounded like relief in his voice. "Is that it? You're ace."

"It's not just-"

"No, no, you're right," Dean continued, cutting Cas off again. "That came out wrong. I don't mean that it is just that. It's just, I was worried, I thought it would be something worrying or bad or- I don't know. I was worried, but you're ace, and that's awesome!"

"What's awesome about being ace?" Castiel's voice was harsh, too much hurt building up from everything he had seen on the internet, all his fears, the fact he knew that he would forever feel like a burden to a partner, because he wasn't- he wasn't normal.

"Whatever you are thinking, stop it right now," Dean said with a glare that could melt ice. "Maybe it's not average, but Cas, you're never average. You're ace, who cares, that's great. Some people aren't attracted to girls, some aren't attracted to boys, you're not attracted to either. That's just how it is. You are perfect the way you are."

"You really think that?"

"Every word. And anyone who says otherwise is either lying, or wrong."

Tears were pooling in Cas' eyes, his friend's acceptance and validation punching him right in the chest in the nicest way possible.

"Thank you," Cas whispered.

"No problem," Dean shrugged, "seeing as we are doing the whole coming out thing, I'm bi. Now come on, let's go watch those movies."

Cas nodded, wiping his eyes. So, Dean was bi. He'd have to come back to that one later, but he could already tell he was going to be thinking about that for the next couple of days - maybe weeks. But for now, they were going to watch movies, it was Halloween, and everything was perfect.


	5. 1997

**31st October 1997**

Cas glared at the Halloween party surrounding him, the so called "sexy" costumes - and some just plain weird ones which left Cas wondering what the wearer was thinking - seemed to be everywhere he looked and he was seriously wondering what he was doing there.

He drained the last of the drink in his red solo cup, wishing that it had been filled with something stronger than slightly spiked punch - did it count as spiked when it was made to be slightly alcoholic? Did it matter? - but unfortunately this party host was either responsable or stupid, but either way hey didn't have anything much stronger than beer, and a single bottle of whiskey that someone else had brought and had been promptly devoured before Cas even arrived at the kitchen.

So now he was standing here, standing like a tree at the edge of the dance floor, wondering if it was too early for him to just leave.

"Hey Cas!" And here he was. The reason Cas was standing in the middle of some stupid Halloween party in way too tight leather pants and cat ears. Why did he ever listen to Dean's costume recommendations?

"Hello Dean. Did you know I hate you?"

Dean burst out laughing, looking like he was about to fall over any moment from how entertaining he was finding Cas' problem alone. "Love ya too Cas," he giggled. "Come on, it's not that bad."

"It really is," Cas groaned, reaching back to grab the tail Dean had stitched to his pants. "I have a tail Dean. And leather pants. What could possibly be good about all this?"

"Well you look amazing." Dean said decisively. "I have at least three reasons which you won't care about unless you have a desire to fuck anyone-"

"No, not today thank you."

"- there we go. And also you will always be able to look back on the day with fondness!"

"I'm wearing leather pants." Cas repeated. "I will never think anything fond about leather pants."

"And I will always stand by the fact it was worth it." Dean grinned. "Maybe not for you, but I have definitely enjoyed it."

"Well good for you," Cas groaned. "But I need more to drink."

"I know where the host keeps their stash of whiskey if that helps?"

"Will they notice it's gone?"

"No, almost definitely not."

"In that case," Cas frowned, looking down at himself and what he was wearing, "lead the way." He waved for Dean to move, needing to get drunk as quickly as possible.

"Are you sure Cas? You know it's not legal for either of us."

"You're eighteen," Castiel shrugged, "we would both be legal if we were in Europe. Let's go."

Dean laughed even more than before, Castiel could kind of understand why. He was normally a stickler for the rules, and certainly the law, but the legal drinking age was mainly just at bars and buying alcohol anyway, and today Cas needed to get pissed before he either killed or kissed Dean.

And sure, maybe taking away rational thinking was not the best way to deal with, and get rid of, these feelings, but it was what he was going to do.

"If I'd known all these years that all it took to break Castiel Novak was getting him to wear leather pants, I would have done this years ago!" Dean quickly shut up when Cas levelled him with a glare, but Cas could tell he was still thinking it.

"I hate you so much."

"You've said."

They walked quickly away from everyone else, finding a couple of bottles of whiskey and then heading out to go looking for an empty room to drink it in. The first couple of ones they checked were occupied, despite the fact the night was only just getting started, but they eventually found an empty room - it looked like some kind of office to Cas, but it wasn't like they were really paying attention to where they were going - and took a seat on the floor.

"Do you want to play a drinking game?" Dean asked, his eyes alight with life.

"No."

"Please!"

"No."

"Come on," Dean whined, "it'll be fun! I bet you've never even played never have I ever!"

"You're right. I haven't. And I never plan to. I just want to get pissed." 

"But you've got to make it fun! What's the point of drinking unless we are playing a drinking game!"

Cas sighed as loudly and as long as he could, glaring at his friend, even as he knew he was about to give in.

"Fine," he muttered, "I know how to play so don't bother with the rules. Just do it."

Dean cheered in a way that was annoyingly endearing, unscrewing the top of the bottle and bit it between them, biting his lip as he thought.

"Never have I ever," he started slowly, drawing each word out, clearly still thinking over what he should continue with. "Never have I ever broken a bone."

"Starting light are you?" Cas asked with a raise of his eyebrow, not drinking.

"You've never broken a bone?"

"You haven't either." Cas pointed out, gesturing to the still untouched bottle.

"Well yeah, but I already knew that. You just seemed like the kind of person who would have broken a bone before!"

"I seem like someone who would be bullied you mean," Cas sighed. "Well, contrary to popular belief, I know how to protect myself. No one bothered coming after me."

"Oh. Well," Dean seemed at a slight loss for words, still looking at Cas like he was trying to figure out what his words meant. "It's your go."

"Never have I ever kissed a girl."

Dean rolled his eyes and took a drink. "Well someone isn't continuing the light tone."

"The game needed to get interesting at some point," Cas shrugged, "I just gave it a head start."

They get halfway through the bottle before their questions start getting more risky. More personal.

"Never have I ever had a crush on a friend." Dean's words were slightly slurred, but Cas understood him clearly enough, the words feeling like a shot through his chest. He'd known this one would come at one point.

Reaching out he grabbed the bottle and took a swig. Once he'd put it back down Dean reached out, also drinking.

They didn't say anything about it, just moved onto the next question, but they shared a look of understanding. They both knew what it was like to love someone who you could never have, and Castiel promised himself that he'd pay attention in the future, see if he could figure out who Dean's crush was. Then again he didn't even know if it was a present day crush, or just a past one.

He still knew he was going to be keeping his eye out for any hint of Dean having a crush.


	6. 1998

**Notes for the Chapter:**

> This was going to be a texting fic... There is... some texting... This fic is a monster. It was not meant to be like this. I love my monster fic child.

**31st October 1998**

Dean stared at his phone, telling himself again and again to just do it, to just pick it up and text and get the ball rolling so that he wouldn't be able to chicken out. He knew what he wanted, and he wasn't going to let himself miss out on it just because he was too chicken shit to give good things a try.

**Dean >>> Hey Cas!**

**Cas <<< Hello Dean. Are you okay?**

**Dean >>> yeah, I'm fine.**

**Dean >>> do you have any plans for tonight?**

**Cas <<< No**

**Cas <<< It's Halloween. I always spend Halloween with you.**

Dean smiled down at his phone, his stomach fluttering at such a simple thing. He liked the thought that Cas counted it as a  _ thing  _ and not just something that sometimes happened. 

He liked it. And hoped that if all things went to plan, he could spend the rest of his Halloweens by Castiel's side.

**Dean >>> perfect**

**Dean >>> meet me at our spot in the park**

**Dean >>> I have a surprise for you.**

Their spot was a little hollow in the woods, far enough in that no one else ever went there, and with enough nature to make it feel like a different world. They had found it during the summer, and had kept on going back whenever they met up.

**Cas <<< okay**

**Cas <<< what time?**

**Dean >>> eight.**

**Cas <<< see you then.**

Dean definitely did not do a little celebratory dance in his seat when he saw that Cas was coming, hope and joy blooming in his chest. Now he just had to hope the rest of the day went as he planned.

Step one done. But that was the easiest one.

He stood up, finding himself bouncing in place as he tried to figure out what to do first. There was so much to do, and so little time to do it, and he just wanted it all to be perfect for Cas.

He needed it to be perfect for Cas.

Grabbing the list he had written a few days ago - he had been planning this for months, and had thankfully been self aware to know that he would be going too crazy with nerves to figure out what to do, and which order to do it in.

"Thank you past me," he hummed, grabbing his coat and his wallet, heading to the shops to grab flowers, food, and some Halloween decorations. Hopefully he'd be able to find everything he needed, and if not, then he would have to do his best to improvise.

It would be perfect. He would make it so.

He was a whirlwind around the shops, going into as many shops as it took to find everything he needed, thanking anything listening when he managed to find the last cowboy hat in the costume section, even if it was pink and sparkly. He could deal with sparkles, and he could already tell it would make Cas grin.

By the time he returned home his legs were tired from walking so quickly, and he had a couple of bags of different things.

"Dean?" His mom appeared in the doorway of his room just as he was fucking everything off his list. "Are you okay?"

"Yeah," he grinned, checking the list for what to do next, even though he already knew what it would be. Pack the picnic.

"What are you doing?"

"Picnic," Dean answered, grabbing the bag of food and starting to head out of his room, hoping the old picnic basket was where he remembered it being.

"For someone special?" Mary guessed, nodding towards the list Dean was still holding, and the small smile which still hadn't left his face. It was a nervous smile, but an excited one too.

"Yeah, I'm going to ask someone to date me," Dean replied, staring at the floor and chewing on his lip while he waited for his mom's reaction.

"Good luck honey," she smiled, pulling him into a tight hug. "You better tell me all about it tomorrow!"

"I will." He promised, almost shocked by how little prying his mom was doing. He'd expected her to try and get all the details as soon as possible.

"Don't worry, I'm sure he'll say yes."

Dean rolled his eyes. Of course. "I can only hope so."

Dean spent the rest of the day getting everything ready, packing their picnic, baking some Halloween cookies, heading to the clearing to decorate it with everything he brought. He finally finished at ten to eight, anticipation making him feel sick, even while excitement made him jittery. He just wanted to finally find out if Cas would want to date him, but first he needed to- woo him, Dean guessed.

"Hello De-" Cas cut himself off, his eyes going wide as he looked around the clearing, taking in the Halloween decorations covering the trees, the blanket Dean was sitting on, the picnic basket in front of him, the sparkly pink cowboy hat on Dean's head.

"Do you like it?" Dean asked, waving his arms to encompass everything he had done.

"Like it? I love it!" Cas gasped, practically floating over to Dean and pulling him into a tight hug. "You did all of this for me?"

"Of course!" Dean grinned, handing over the angel halo he'd bought for Cas, and rummaging through the basket to find their food.

"From our first meeting," Cas whispered, his eyes flickering from the halo to the cowboy hat, back and forth again and again.

"Thirteen years ago," Dean whistled, "lots has changed since then."

"But not our friendship," Cas grinned, "that will always stay strong."

Dean smiled back, unable to not in the face of Cas' pure joy.

"About that," he said very slowly, making eye contact with Cas and making sure he had the other boys - other man's. They were adults now. A lot had changed - full attention.

"Dean?"

"Cas, willyougooutwithme?" Dean had meant to say it slowly, but not everything could go to plan, and he'd just needed to get it out there before he combusted.

"Are you- are you asking me to be your boyfriend?" Cas asked, barely hidden hope flashing in his eyes.

"Yes I am. Will you?"

"Yes. I will be your boyfriend Dean Winchester."

They held eye contact for a long moment, drifting towards without even thinking about it, meeting in the middle in a soft kiss before either of them even noticed they were moving.

"Best treat I've ever gotten," Dean whispered when they pulled back for breath, getting a huff of laughter from Cas in response, and then another long sweet kiss.

It was definitely better than any candy.


	7. 2020

**Notes for the Chapter:**

> I did it!! Time to sleep me thinks. Thanks for reading!!

**31st October 2020**

Castiel leaned out the window, breathing in deeply to smell the cool air, getting the unmistakable smell of fall which was heavy in the air deep into his lungs. It made him feel alive, reminded him of the best times of his life. 

The pumpkins which Jack and Claire had carved earlier - the reason Cas had come outside in the first place - were flickering away happily on their wooden porch, lighting a small amount of the decking around them as the tea lights managed to stay lit even with the wind doing its best to blow them out. He could hear excited voices from the kitchen, and knew that Dean and the kids would be in there baking their traditional Halloween treats which only seemed to get more delicious every year.

He had helped them carve the pumpkins, doing most of the actual carving for Jack - who was way too young to be given a knife for carving, but had seemed quite happy to just mess around with the seeds - while taking on a more advisory role with Claire, who could easily carve on her own, and just needed a bit of help with the logistics of her designs sometimes. Cas had just put them out on the porch after they spent the morning sitting in the kitchen, but he didn't feel like going back inside yet.

Instead he leaned against the porch railing, leaning his head back to stare up at the clear sky, the large full moon shining up in the sky, bright enough to give Castiel enough light to vaguely see his surroundings.

This Halloween wasn't like other ones, the world was such a mess that he'd almost forgotten their family's favourite holiday, the year going by in the blink of an eye even as it felt like it was lasting forever. It felt like it should be December already, while also feeling like the middle of March. It was just weird, though there wasn't much confusion what date it was right now with all the pumpkins and skeletons.

A particularly loud giggle came from the open kitchen window, dancing in the silence of the night and bringing a small smile to his face. He was happy with his life, glad that this was what the universe had given him, after everything.

Castiel wasn't sure if he believed in a higher being, and had never thought he believed in soulmates. But if he had one, it was Dean Winchester-Novak.

His husband was perfect for him, and had absolutely changed his life.

Cas had hated Halloween as a very small child. He could barely remember it any more, just a few memories of how much he'd hated it, but his earliest vivid memory was of Halloween before he had even started school, how even at that age he thought it was a waste of time, and he just wished it was over already.

And then a slightly younger boy in a cowboy costume with an almost lost hat had all but adopted him, dragging him into the joy of the holiday, showing him how much fun it was. Once Dean had shown him how good it was, he started finding the joy everywhere. 

His family's traditional trip to the pumpkin carving avent had always seemed so stupid, but after that day meeting Dean, he'd realised how much fun it was - though none of thome times he went with just his family were anywhere near as fun as any of the times he went there with Dean.

Suddenly dressing up wasn't a chore, and trick or treating wasn't a pain, and pumpkin carving wasn't just a mess, and although parties were still stupid, they were fun while Dean was there.

His life would have been nothing like his present one if he'd never met Dean. It wouldn't have been as fun, as happy, as fulfilling. He wouldn't have two beautiful kids, a loving marriage, and a million happy memories to go with Halloween.

He wouldn't have the love of his life.

"You look like you're thinking heavy thoughts," Dean said from just behind him, walking over to lean on the railing next to his husband, a blissful smile on his face when he closed his eyes and breathed in deeply.

"I'm just thinking of how much I love you," Cas replied honestly. "Through all these years all you have done is make my life so much better, I don't know how to ever thank you for that."

Dean laughed, wrapping his arms around Castiel's waist, burying his face into Cas' neck. "You don't need to thank me," he told Cas fondly. "You've given me as much as I've given you. That's what we do. We love, and we give, and we be happy together."

"Who are you and what did you do with my husband?" Cas asked teasingly, "the real Dean is never that profound."

"Nah, I normally leave that up to you don't I?" Dean pressed a gentle kiss to the skin of Cas' neck in front of his mouth, and Cas could feel Dean smiling.

"Where are the kids?" Cas asked, leaning into Dean and enjoying the quiet of night, quiet voices from the house telling him that they were still inside.

"Watching A Nightmare Before Christmas," Dean replied with a fake shudder, "apparently they agree with you about it being a Halloween movie."

"You're just bitter that we are right," Cas teased, bopping Dean on his nose.

"It's a November movie!" Dean argued, lifting his head to stare at Cas, "It has both Halloween and Christmas in it!"

Castiel smiled fondly. Dean was adorable when he got rilled up over the silly things. "Okay dear."

Dean huffed, dropping his head back against Cas' chest. "Stop doing that!"

"Doing what?"

"Using pet names to win arguments!"

Castiel held back a laugh, smiling innocently at Dean. "But sweetheart, it's not my fault if you haven't got used to it after over twenty years!"

"They're my weakness okay! You can't blame me for that!"

"I can try."

They just stood there for a long moment, enjoying each other's warmth and love, rocking in place a little as they clung to each other.

"It's October 31st," Dean whispered, "Seems like a good time to remind you that I love you."

Cas pressed a fond kiss against Dean's head. This was one tradition he had never hated, and would never get bored of.

"It's Halloween," he whispered back, "I hope you don't need reminding, but just in case you do, I need to tell you that I love you."

**Author's Note:**

> Thank you so much for reading!!! I hope you enjoyed!!  
> Kudos and comments mean the world to me!!  
> Have a very happy Halloween!! And an awesome November!!!


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